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WO2007041167A3 - Procédé pour la production de delta-9-tétrahydrocannabinol - Google Patents

Procédé pour la production de delta-9-tétrahydrocannabinol Download PDF

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Publication number
WO2007041167A3
WO2007041167A3 PCT/US2006/037709 US2006037709W WO2007041167A3 WO 2007041167 A3 WO2007041167 A3 WO 2007041167A3 US 2006037709 W US2006037709 W US 2006037709W WO 2007041167 A3 WO2007041167 A3 WO 2007041167A3
Authority
WO
WIPO (PCT)
Prior art keywords
compound
delta
tetrahydrocannabinol
substituted
relates
Prior art date
Application number
PCT/US2006/037709
Other languages
English (en)
Other versions
WO2007041167A2 (fr
Inventor
David C Burdick
Steven J Collier
Frederic Jos
Betina Biolatto
Bernhard J Paul
Harold Meckler
Mark A Helle
Alicia J Habershaw
Original Assignee
Amr Technology Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Amr Technology Inc filed Critical Amr Technology Inc
Priority to JP2008533571A priority Critical patent/JP2009510078A/ja
Priority to NZ594077A priority patent/NZ594077A/xx
Priority to AU2006297300A priority patent/AU2006297300B2/en
Priority to CA002623723A priority patent/CA2623723A1/fr
Priority to NZ567029A priority patent/NZ567029A/en
Priority to EP06804207A priority patent/EP1928853A4/fr
Publication of WO2007041167A2 publication Critical patent/WO2007041167A2/fr
Publication of WO2007041167A3 publication Critical patent/WO2007041167A3/fr
Priority to IL190388A priority patent/IL190388A0/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrane Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé pour la préparation d'un composé delta-9-tétrahydrocannabinol ou d'un dérivé de celui-ci comprenant de traiter un premier composé intermédiaire avec un catalyseur de type acide de Lewis à base d'organoaluminium, dans des conditions efficaces pour produire le composé delta-9-tétrahydrocannabinol ou le dérivé de celui-ci. Un autre aspect de la présente invention concerne un procédé pour la préparation d'un composé cannabidiol ou cannabidiolate comprenant de faire réagir un premier composé de départ avec un second composé de départ en présence d'un catalyseur de type triflate de métal, dans des conditions efficaces pour former le composé cannabidiol ou cannabidiolate. La présente invention concerne également un composé de formule (I) : où R8, R9 et R10 sont identiques ou différents et sont chacun indépendamment sélectionnés entre H, un alkyle substitué ou non substitué, un aryle substitué ou non substitué, un hétéroaryle substitué ou non substitué ou un halo, R1, R2 et R3 étant définis ici.
PCT/US2006/037709 2005-09-29 2006-09-28 Procédé pour la production de delta-9-tétrahydrocannabinol WO2007041167A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP2008533571A JP2009510078A (ja) 2005-09-29 2006-09-28 Δ−９−テトラヒドロカンナビノールの生成法
NZ594077A NZ594077A (en) 2005-09-29 2006-09-28 Process for production of delta-9-tetrahydrocannabinol
AU2006297300A AU2006297300B2 (en) 2005-09-29 2006-09-28 Process for production of delta-9-tetrahydrocannabinol
CA002623723A CA2623723A1 (fr) 2005-09-29 2006-09-28 Procede pour la production de delta-9-tetrahydrocannabinol
NZ567029A NZ567029A (en) 2005-09-29 2006-09-28 Process for production of delta-9- tetrahydrocannabinol
EP06804207A EP1928853A4 (fr) 2005-09-29 2006-09-28 Procédé pour la production de delta-9-tétrahydrocannabinol
IL190388A IL190388A0 (en) 2005-09-29 2008-03-24 Process for production of delta-9-tetrahydrocannabinol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US72203105P 2005-09-29 2005-09-29
US60/722,031 2005-09-29

Publications (2)

Publication Number Publication Date
WO2007041167A2 WO2007041167A2 (fr) 2007-04-12
WO2007041167A3 true WO2007041167A3 (fr) 2007-11-22

Family

ID=37906689

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/037709 WO2007041167A2 (fr) 2005-09-29 2006-09-28 Procédé pour la production de delta-9-tétrahydrocannabinol

Country Status (11)

Country Link
US (3) US7674922B2 (fr)
EP (3) EP1928853A4 (fr)
JP (1) JP2009510078A (fr)
KR (1) KR20080063800A (fr)
CN (2) CN102766128A (fr)
AU (1) AU2006297300B2 (fr)
CA (1) CA2623723A1 (fr)
IL (1) IL190388A0 (fr)
NZ (3) NZ601567A (fr)
WO (1) WO2007041167A2 (fr)
ZA (1) ZA200802767B (fr)

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ZA200802767B (en) 2009-09-30
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US7674922B2 (en) 2010-03-09
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US8106244B2 (en) 2012-01-31
CN101316832A (zh) 2008-12-03
US20110263878A1 (en) 2011-10-27
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US20070093665A1 (en) 2007-04-26
CA2623723A1 (fr) 2007-04-12
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JP2009510078A (ja) 2009-03-12
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EP2578577A1 (fr) 2013-04-10
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